Chitown Politics

On Monday, Cheryle Jackson, in that odd modern political maneuver, announced that next month she would announce her candidacy for the US Senate race.  Meanwhile, she’s still serving as president and CEO of the Chicago Urban League– at least according to its website. Her dual role of candidate and nonprofit executive could be confusing. When she appeared at Wednesday’s Chicago 2016 fundraiser (she sits on the bid committee board), was it as a nonprofit leader or as a candidate? When Chicago Urban League corporate funders met with her that day, did they imagine they were talking to nonprofit partner or a potential Senator? Presumably, Jackson will step aside from her day job next month when she officially announces, but until then our questions stand. One wonders what the Urban League’s board (a who’s who of powerful Chicagoans, including Bill Daley, John Rogers and Chicago Public Schools Chairman Michael Scott. [Scott has been in the news lately.]) We can’t think of a recent example of a nonprofit CEO running for political office. (In 2007, Newt Gingrich cited his leadership of American Solutions as a reason not to run for President. Jesse Jackson ran for the White House in 1984 while leader of Operation Push.)

Also on Monday, wealthy Northshore entrepreneur Kip Kirkpatrick announced his candidacy for Treasurer. A Democrat (albeit one who supported Republicans Mark Kirk and Rudy Giuliani in the ‘08 cycle, as well as Rahm Emanuel’s PAC), Kirkpatrick co-founded the private equity firm Water Street Healthcare Partners in 2005. Unlike Jackson, Kirkpatrick seems to have divorced himself from his employer, as he is no longer listed on Water Street’s masthead. (Dan Primack of Private Equity Hub explored the potential complications for Water Street should Kirkpatrick win. He garnered a statement from WSHP that it “will not solicit money from any Illinois state pension fund if [Kirkpatrick] is elected to the treasurer position.”)